Sales Training & Enablement Manager

At Pro Service, we empower employers to succeed in Hawaii. For more than 30 years, local businesses have trusted us with their payroll, HR, and benefits, and our sales team is how they find us. As we grow, the way we develop our sellers matters more than ever.

As Sales Training & Enablement Manager, you'll formalize how every Pro Service seller is onboarded, certified, and upskilled, from SDRs to SBO and Mid Market Business Development Managers to our channel team. Your biggest focus will be value selling: helping reps explain how our full bundle, from healthcare to payroll, workers' compensation, HR, and technology, saves businesses money and makes running them easier.

Success means a certification program ready for our 2027 hires and clear proof that training is working, such as hearing reps apply value selling on their Gong calls within weeks of completing a program.

IN THIS ROLE YOU WILL

Design, launch, and improve role-based onboarding, ramp plans, and certification for SDRs, BDMs, and channel sellers, replacing ride-along learning with a structured path

Build a value selling curriculum on the Pro Service bundle, partnering with Marketing and Product to turn our healthcare offerings, aligned pricing, and service model into a clear value story

Create digestible, testable training materials with role plays, assessments, and certifications that confirm reps can apply what they learn

Deliver ongoing training on prospecting, discovery, qualification, proposals, objection handling, and negotiation tailored to each sales motion

Measure impact in Gong and Salesforce, including whether reps use value selling language on calls after training, and report results on ramp time, conversion, and quota attainment

Partner with sales leaders on coaching standards, call reviews, and manager guides so training sticks in the field

IS THIS ROLE RIGHT FOR YOU?

This role drives results through people you don't manage, and it is measured by application, not attendance. Earning credibility with experienced sellers, building materials reps actually use, and proving with Gong and Salesforce data that behavior is changing are not optional — they're the job. You'll have the partnership of sales leadership, Sales Operations, Marketing, and Product.

Many of our reps learned by riding along with a colleague, so you'll be building much of this from the ground up, and quickly, to support a wave of 2027 hires. Pro Service sells a complex offering to very different buyers, so one-size-fits-all training won't work. If you prefer to deliver polished content and move on, this may not be the right fit.

If you want to turn the way our best sellers win into a repeatable, measurable system, this role offers real impact.

WHAT YOU’LL BRING TO THE TEAM

You've built and run a sales onboarding, certification, or training program that measurably shortened ramp time or improved results, and you've carried a quota or sold B2B services yourself, ideally in PEO, HR, payroll, benefits, insurance, or professional services. You bring hands-on experience teaching value selling, strong coaching and presentation skills, sharp analysis, and the ability to lead change and inspire sellers to adopt new habits.

You're probably a fit if:

You've replaced ride-along onboarding with a real program. You built a structured certification path, and new reps walked into their first prospect meetings confident instead of overwhelmed.

You teach value selling that shows up on calls. After a six-week value selling program, you heard reps leading with business outcomes on their Gong calls instead of price, and prospects started asking deeper questions about the full offering.

You turn cross-functional knowledge into training reps can use. You pulled product and…